


Topsy-Turvy

by anotsosecretfangirl



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Roommates/Housemates, Anal Fingering, Anal Sex, Bottom Dean, Dean in Panties, Friends to Lovers, Hand Jobs, M/M, Misunderstandings, Panties, Panty Kink, Plot What Plot/Porn Without Plot, Rimming, Smut, Strangers to Friends to Lovers, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2017-01-13
Updated: 2017-01-13
Packaged: 2018-09-17 07:38:49
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,045
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9311843
Author URL: https://archiveofourown.org/users/anotsosecretfangirl/pseuds/anotsosecretfangirl
Summary: Castiel has to survive Gabriel's visit and Dean offers to stay over for moral support, however when Dean's curiousity gets the better of him, things take an (expectedly) unexpected turn.





	1. Chapter 1

**Author's Note:**

> Hey guys! I started writing this when in saw a prompt regarding how your OTP met (which is basically the first half of the first chapter) and I guess I just kept writing my mindless thoughts, so I realize some situations might be a bit unrealistic, but then again, it's just a story.  
> Happy reading! :)

"Cas, hey, it's good to see you man, come on in," Sam steps back from the doorway and Castiel passes over the threshold and into the house. He awkwardly stands there for a moment, before Sam motions him into the kitchen.  
"You can set up your laptop on the counter, let me just quickly grab my notes and laptop from upstairs and then we can get to work," Castiel nods and Sam disappears upstairs to retrieve his things.  


He had just taken out his work when he hears footsteps coming down the stairs. He looks up, expecting to see Sam, but instead he is faced with a shirtless, muscular man with short, dark blonde hair: definitely not Sam. Castiel is at a loss with what to do. Should he announce his presence and risk embarrassing the man? What if it his presence elicits an unwarranted response? Sam never mentioned having a roommate, so perhaps this was his boyfriend?  


The man walks over to the fridge, still blissfully unaware of the other's presence, and starts raiding the fridge. When he turns around the sight of Castiel startles him, causing him to jump and drop the food, which had previously been stacked up to his chin, in the process. Castiel desperately tries to stifle a laugh, but he can't help but find the situation amusing. The man becomes visually flustered, a blush creeping up his freckled face.  


"What the hell?! Warn a guy, would ya?!" Castiel sobers up,"I apologize, it was never my intention to scare you."  
The man scoffs,"You didn't scare me, you just startled me, that's all. And, to be fair, it's not like I was expecting to see a hot guy sitting at my kitchen counter." This time it's Castiel's turn to blush. Luckily he is saved from responding, as that's the moment Sam enters the kitchen.  


"Hey Cas, sorry for taking so long, I couldn't find my laptop cable. I hope Dean here hasn't given you too much trouble, he can be a real handful sometimes, and Dean," he sets his things down on the counter and turns towards Dean,"please clean up this mess before you go." Castiel is a bit disappointed when Dean leaves, but if he's honest with himself, he knows he won't be able to focus with the shirtless man around, besides, he doesn't know what kind of relationship Dean and Sam has, so it would be quite inappropriate to let his thoughts run away with him.

They work on their assignments for a while, until Castiel's stomach starts voicing it's complaints, so they decide it's time to take a breather. "Do you want to order pizza? Dean should be on his way home by now, so I can call him and ask him to pick it him," Sam turns to Castiel expectantly and he concedes that he probably won't be able to get any more work done on an empty stomach. Sam practically beams at him and Castiel can't help but feel like Sam's enthusiasm is contagious. "Awesome, I'll let Dean know." After Sam texts Dean, Castiel can't help but let his curiosity get the better of him.  


"I didn't know you have a roommate," Castiel states as casually as possible, though to him it sounds a little bit forced, but if Sam notices, he doesn't mention it.  
Sam laughs. "I guess you could call him that. I just can't believe Dean hasn't come up in conversation before, I mean we've been friends for a while now. Dean's my brother."  
"Oh, well from what I've seen of him, you guys don't seem that much alike."  
"Says the guy who's related to Gabriel," Sam teases. Castiel groans,"Please don't remind me. I still have a scar from the last time he visited, excluding the mental ones." "You have to tell me what he did this time," Sam pleads.  


"Let's just say it involves panties, and is also the reason I don't have a roommate anymore," Castiel shudders at the memory.  
"Please," Sam begs, giving him puppy dog eyes.  
He relents, but before he could start the story, Dean arrives with the pizza.  
"That was quick," Sam remarks.  


Dean gives him a sheepish smile,"I might've stopped for pizza before you asked." He puts the pizza down on the table and plops down next to Castiel. "So what were you two old ladies talking about before I blessed you with the gift of pizza?" Dean asks.  


Castiel's brows furrow,"I am not an old lady." The brothers both laugh and Castiel sends them a scrutinizing look, but before he can say anything else, Sam interjects,"Castiel was just about to tell me the story of why his roommate moved out, apparently it involved his brother and panties." Dean quips a brow,"Panties?" Castiel groans internally. This is definitely not a stranger he wants to tell a guy he's just met, and he voices his concerns to Sam.  


"You caused me to shriek like a girl before even speaking a word to me, an embarrassing story would put us on even grounds," Dean states, as if it's the most logical thing in the world. Castiel sighs and starts telling the story of how, after he lost a bet, he was forced to cook breakfast for Gabriel, wearing nothing but panties, which would've been fine on its own, since Gabriel would relish in his humiliation and then quickly tire of it, but what he hadn't anticipated was his roommate coming home so soon. 

He had hid in his room for some time after, only to discover that Gabriel had put superglue at the back of the waistline, resulting in both a mental and physical scar from his visit, though looking back on it he doesn't know how he didn't notice it sooner. All in all his roommate had been pretty chilled about the situation, but Gabriel kept tormenting Castiel in the weeks to come, sending him packages from Victoria's Secrets and he even went so far as to send cupcakes decorated with panties on them. Eventually his roommate had had enough and decided to move out; when he told Gabriel this, he was quite smug and deemed it an achievement; Castiel had been living on his own ever since.  


"Wow, your brother sounds horrible," Dean laughs.  
"Tell me about it, and now he's decided to come down next weekend and I honestly don't think I'll be able to survive it unscathed. At least when I had a roommate he toned it down a bit."  
"I'd offer to stay with you while he's here, but Charlie and I are road tripping that weekend," Sam says apologetically.  
"You know," Dean starts,"I could play your fake roommate for the weekend, since Sammy's not here anyway," Dean offers.  
Castiel turns to Sam, as if asking for his blessing, and Sam simply shrugs; having met Gabriel he knows that Castiel will need all the help he can get.


	2. Chapter 2

That's why a week and a bit later Dean's at his doorstep with his duffle bag. He invites him in and shows him around. The apartment has a basic floor plan, with the two bedrooms being perpendicular to each other, with a single bathroom being adjacent to one of the bedrooms.  
Castiel offers Dean a beer, which he readily accepts, and allows him to settle in. Dean emerges from the spare bedroom a while later holding a package, and then it dawns on him that it's the package.  


"Dean, I'm so sorry, I can explain, I forgot I left that in there..." Castiel's rambles stop when he realizes Dean isn't looking at him with eyes filled with disgust, but rather an expression filled with curiosity.  
"I wasn't snooping or anything, I was just unpacking my clothes when I found it in the cupboard," Dean hesitates,"and I was wondering if I could try them on?"  


Castiel's eyes go wide, out of the things he had expected Dean to say, that definitely wasn't one of them. "You know what, forget I mentioned it, it was a stupid idea anyway," Dean turns to head back to the bedroom, but Castiel stops him. "There's another package under the bed if you want to try on those as well." Dean gives him a weak smile and disappears into the bedroom. 

When Dean's out of sight, Castiel can't help but him in the piece of scantily clad fabric, bent over his table, begging Castiel to fuck him; Castiel chastises himself, for all he knows Dean could be straight, after all, tastes are quite versatile; he's ripped from his thoughts when Dean enters the living room, clad in nothing but a pair of green lace boyshorts, which barely covers his package. Castiel's mouth goes dry and he has to resist the urge to reach out and touch the other man. 

Dean gives a little twirl, a hint of mischief shining in his eyes,"So, what do you think?" Castiel gapes at him, opening and closing his mouth like a goldfish. "You..you look good," Castiel says with a strained voice.  
"Hmm," Dean sounds in agreement,"and it's really quite soft." 

Dean runs fingers tips over his thigh, gently caressing the material. Castiel struggles to tear his eyes away and can feel his pants growing so tight that it's causing him discomfort. "Would you like to touch it?" Castiel is dumbstruck, but when he gets his wits about him, he doesn't hesitate to take it as an invitation. 

His hand is shaking when he sticks his arm out, his fingers tracing circles over his pantry clad thigh. Dean's breath hitches when Castiel's fingers graze his crotch area; having grown visibly hard the fabric is straining over his member. Castiel now traces the outline of his crotch, every so often running his hand over it, every so often drawing a moan from Dean. 

When he can't resist the temptation any longer, he fondles him, moving his hand slow and deliberately over his covered shaft. Dean whimpers, but before he's able to slip his hand into his underwear, Dean pushes a bottle of lube into his hand. Castiel blushes, having not even noticed him carrying it previously, but in all fairness Dean was posing to be quite the distraction. He lathers his hand in lube and takes him in his hand, pumping up and down and every so often circling his thumb over his head, using his other hand to fondle his balls. 

Dean thrusts into his hand and Castiel's finger circles over his pucker, never ceasing his other administrations. He puts some more lube on his fingers and pushes one in, moving in and out of him, croaking his finger inside of him, soon joined by another. When he locates Dean's prostate he rubs against it, causing Dean to moan his name, practically sobbing. Castiel withdraws his fingers and pushes them in again, along with a third, and thrusts in and out of him. Dean clenches down on his fingers and thrusts erratically into his hand, achieving his climax and soiling the green fabric in the process. Castiel withdraws and brings his cum-stained hand to his lips, licking up the mess and moaning appreciatively.  


"You are far to sexy for your own good," Dean says.  
They end up in the shower, where Dean process to give Castiel a soapy handjob. He barely touches him and already he's sent over the edge, spilling all over Dean's hand. They wash each other in a strangely intimate moment and once their clothed again there's an awkward moment where neither seems to know what to do about their rooming situation. Castiel's the one that breaks the ice and takes Dean's hand, dragging him into his room. They climb under the covers and Castiel throws his arm over Dean's waist, pulling him closer so that their bodies are pressed flush against each other. He gets the feeling that Dean wants to protest, but he soothes him by kissing the back of his neck, feeling the other man become pliant in his hold.


	3. Chapter 3

Castiel is awoken by a loud thud, followed by Dean cursing and the sounds of a struggle. He jumps up and runs into the kitchen, only to find Dean pinning Gabriel to the counter. Castiel doesn't even bother stifling his laugh. "I see you've met my brother," Castiel chuckles. Dean looks at him incredulously,"This is Gabriel? Somehow I thought he'd be...bigger."  


Gabriel squirms under Dean's hold,"Hey, I'm right here! Cassie, can you please call off your boy toy?"  
"Gabriel," Castiel says in a warning tone, though Dean lets go regardless.  
Gabriel turns to glare at both of them and Castiel pours himself a cup of coffee,"You're early," he remarks.  
"I wanted to surprise my darling younger brother, being attacked by a caveman wasn't on my agenda."  


Castiel rubs his temples, already he's developing a headache and Gabriel just got here,"Gabriel, this is my roommate, Dean."  
Gabriel snorts,"Roommates? Is that what kids are calling it these days? I mean as far as I know roommates don't sleep in the same bed, and Dean-o here definitely didn't come out of his own room. So tell me, Cassie, how did you meet your 'roommate'?" Castiel is spared from answering as Dean decides to step in,"Well I guess you could say he had me screaming before he even knew my name," Dean smirks and Castiel chokes on his coffee. For a moment Gabriel seems at a loss for words, but quickly composes himself.  


"Kinky Cassie, never knew you had it in you. Though, to be fair, it does seem like Dean wears the pants in your relationship," Castiel doesn't know how to respond, he'd always had to endure Gabriel's teasing, but normally it wasn't focused on his sex-life (and when it was, it was normally focused on the lack thereof).  


"Personally I prefer both of us pants-less, though I suppose you are somewhat correct, as I am the one who wears the panties in our relationship," Dean says shamelessly and winks at Castiel. He's surprised at how well he's handling Gabriel and can't help but wish that they had a relationship. 

If Gabriel responds he doesn't hear it, having decided to opt out of the conversation in favor of a hot shower. He tosses his dirty clothes in the laundry basket, smirking when he spots the pair of green cum-stained panties. He washes himself and gets dressed, emerging from the bathroom feeling refreshed and awake. 

He finds Gabriel chewing down on a piece of bacon and raises an eyebrow at the sight, in all the years that he's known Gabriel he doesn't think he's ever seen the man make breakfast. "Okay Cassie, I decided I like him, you can keep him," he says cheekily as he tears off another piece of bacon. Castiel smiles, somehow whilst he was showering Gabriel and Dean had reached some sort of agreement, and, knowing Gabriel, it normally takes more than a few strips of bacon to make that happen, but he decides to count his blessings and doesn't question it, he's due for a win anyway.  


"Where is Dean anyway?" Castiel asks.  
Gabriel shrugs," He said something about picking up his baby; he said he'll be back tonight though, but to be completely honest with you, I wasn't really paying that much attention." Castiel's blood runs cold. He didn't know Dean has a child, and Sam never mentioned it either, then again he only recently started talking about Dean. 

Did he just not want him to know he has a baby, or did he just not mention it because he doesn't see them being in a long term relationship? Oh god, what if Dean was already in a relationship and he's cheating on them with Castiel? Despite him wanting to do nothing more than go back to bed and wallow in self-pity, he pulls himself together and uses Gabriel as a distraction. "What do you want to do today?" He asks Gabriel. 

When they finally get home that evening he's exhausted. Gabriel spent the day dragging him from candy shop to candy shop and took his time exploring numerous bakeries. On the bright side he hadn't thought about Dean all day, but he knows it's time to face the music, rather now before he becomes too invested. He opens the apartment door and is met with a whiff of hot-air coming from the kitchen. He follows the delicious scent, only to find Dean in the kitchen, wearing his girly pink apron which Gabriel got him as a gag gift. All in all the scene appears to be quite domestic.  


"Hey guys, how was your day? I hope you guys are hungry, I'm making burgers." Dean looks so cute and for a moment he forgets he's a possible adulterer, but he refuses to delude himself that he can be part of his world. "So Dean, did you pick up your baby?" Castiel bites out. Dean raises a brow, but doesn't comment on it, instead letting face break into a smile,"I did, she looks good too, got her cleaned up real nice," Dean practically beams.  


"Oh, where is she now?" Castiel asks.  
"She's in the parking lot," Dean answers smoothly, and Castiel can hardly believe what he's hearing, how careless can one person be?  
"The parking lot?" He asks incredulously.  
"She sure is. Would you like to meet her? The burgers are just about done anyway." 

Castiel gives a tight lipped smile and nods. They walk down to the parking lot, leaving Gabriel to his own devices upstairs. Dean comes to a halt in front of a black, vintage looking vehicle.  
"Cas, meet Baby," he says, stroking lovingly over the vehicle,"she's a beaut, ain't she? 1967 Chevy Impala. She use to belong to my dad." Castiel has never felt like such an idiot. Baby is a car. Instead of responding he pushes Dean against the hood of the car and lets his lips devour the other man's. Dean's lips feel soft and warm against his own chapped lips and all to soon he pulls away, resting his forehead against Dean's. 

They had really done everything backwards, he realizes, as it dawns on him that this is the first time that they actually kissed. Dean nibbles at his jaw and nips playfully at his earlobe,"I'd love for you to strip me down and fuck me, right here, on the hood of the car, slowly having me come undone, forcing me to beg you to nail me harder," he whispers into his ear and Castiel can feel himself getting harder at the thoughts which Dean put into his head. 

Before he can act on them though, Dean pushes him away,"and as much as I want that, it's going to have to wait. The burgers are getting cold and you probably don't want to leave Gabe alone for too long." Dean is such a tease and it takes everything in Castiel's power to will his erection away. Before they reach the door he pulls Dean to the side. For the entire day he had stupidly believed that he has a child, so to avoid any further misunderstandings he needs to clarify one last thing.  
"Dean, are you seeing anybody?" He asks, training his eyes on Dean. Dean looks at him accusingly,"What the fuck? Of course I'm not seeing anybody. Do you think I'd even be here if I were?"  


Castiel looks down at his feet,"To be honest, for the majority of the day I thought Baby was an actual baby, so I just had to make sure."  
Instead of being mad, he laughs," Cas, I can promise you, that to my knowledge at least, I have no kids and I'm definitely not seeing anybody at the moment."  
"Would you like to? See somebody I mean? Me in specifically."  
Dean gives him a bemused smile,"Cas, are you asking me to go steady?"  
Castiel rolls his eyes,"Yes Dean, I'm asking you to go steady."  


Dean pulls him into a kiss,"While if you put it like that, how can I refuse?"  
They enter the apartment holding hands, only to find Gabriel devouring which appears to be his second, or maybe third, burger. Instead of chastising him for not waiting for them, he simply takes the seat next to Gabriel and eats his own burger, moaning with appreciation as the flavor hits his tongue. Dean's cheeks flush red and Gabriel clears his throat,"Do you want us to leave the room?" He teases. 

Castiel tilts his head in confusion,"Why would I want you guys to leave the room?"  
Dean laughs,"Nothing Cas, just shut up and eat another burger." Castiel shrugs it off and does as he's told, though he doesn't need any encouragement to eat another burger anyway. He feels really happy and is still smiling when he's doing the dishes. Their relationship so far has been topsy-turvy, but he finally feels content and won't have it any other way.


	4. Chapter 4

After watching some superhero movie (if Castiel's being honest, he wasn't really paying that much attention, as he kept getting distracted by Dean, his face was just so animated and instead of being engrossed by the movie, he was hypnotized by Dean) Dean and Castiel retired to the one room while Gabriel took the other. 

Once he closes the door, Dean pushes Castiel against the wall and kisses his neck, sucking at his collarbone,"You made such filthy noises at dinner, I almost stripped you right there, in front of your brother." Castiel is clearly affected by Dean's words and runs his hands over Dean's back, tugging at the affronting material. Dean quickly gets with the picture, stripping off his shirt and taking off Castiel's as well. 

They move to the bed and he runs his fingers over Castiel's torso,"Your beautiful," he murmurs against Castiel's skin, licking down and taking a nub into his mouth and biting lightly, causing him to arch up. Dean quickly removes their pants and underwear and retrieves a bottle of lube from his bag. "Really Dean?" Cas teases. 

Dean shrugs,"It pays to be prepared." He slicks up his fingers and starts working himself open, squirming on top of Castiel. When he's ready he slowly starts impaling himself on his cock, enwrapping him in a tight heat. He bottoms out and when Dean adjusts he starts to move. Dean bounces himself up and down on his lap. Castiel flips them over, the new position giving him much more leverage, allowing him to nail Dean's prostate head on. 

He pulls out almost completely and thrusts in hard, causing Dean to moan. He repeats the action a few times and then switches to quick, shallow thrusts. He takes Dean's cock in his hands and pumps once, twice and then Dean spills all over their stomachs. His walls clenches around him and he continues to fuck Dean through his orgasm, chasing his own release. It's when Dean moans out his name that he comes undone. 

"Dean," he cries out and shoots his cum inside of him. He pulls out and moves down Dean's body, prodding at his entrance with his tongue, tasting his own release. He pushes his tongue in and out of him, lapping up the cum, all the while causing Dean to whimper and groan. 

Once he's satisfied, he fetches a cloth and cleans them up, tossing the rag away when he finishes. He kisses Dean, slow and surely, this time not fueled by lust, but rather a growing affection. He pulls Dean closer and holds him tight, afraid that if he lets him go he'll lose this moment forever. 

The next morning Gabriel barely looks them in the eye, much to Castiel's great pleasure. When the doorbell rings Gabriel practically leaps up and runs to the door, swinging it open.  
"Hey Gabriel," greets Sam.  
"Dude, you look horrible. I'm Charlie by the way."  
"Firstly, hello Samsquatch, and secondly," he says, turning to Charlie," the reason I have bags under my eyes is because your brother," he points accusingly at Sam,"and my brother are extremely vocal in bed."  
Charlie turns to Sam, grinning shamelessly,"Looks like you owe me lunch."


End file.
